JP2005515217A5 - - Google Patents

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Publication number: JP2005515217A5
Authority: JP; Japan
Prior art keywords: solvent mixture; decapeptide; nonapeptide; precipitation; alcohol
Prior art date: 2002-12-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP2003556430A

Other languages

English (en)

Japanese (ja)

Other versions

JP2005515217A (ja

JP4378173B2 (ja

Filing date

2002-12-23

Publication date

2005-12-22

2001-12-29 Priority claimed from SE0104462A external-priority patent/SE0104462D0/xx

2002-12-23 Application filed filed Critical

2005-05-26 Publication of JP2005515217A publication Critical patent/JP2005515217A/ja

2005-12-22 Publication of JP2005515217A5 publication Critical patent/JP2005515217A5/ja

2009-12-02 Application granted granted Critical

2009-12-02 Publication of JP4378173B2 publication Critical patent/JP4378173B2/ja

2022-12-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
238000000034 method Methods 0.000 claims description 24
238000001556 precipitation Methods 0.000 claims description 18
239000011877 solvent mixture Substances 0.000 claims description 18
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 14
239000012156 elution solvent Substances 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
229940124041 Luteinizing hormone releasing hormone (LHRH) antagonist Drugs 0.000 claims description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 4
239000002474 gonadorelin antagonist Substances 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
238000000746 purification Methods 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
RMOUBSOVHSONPZ-UHFFFAOYSA-N Isopropyl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 claims description 2
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
238000001035 drying Methods 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 2
FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 2
OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 2
229940017219 methyl propionate Drugs 0.000 claims description 2
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
-1 t- butyl Chemical group 0.000 claims description 2
238000005406 washing Methods 0.000 claims description 2
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
108090000765 processed proteins & peptides Proteins 0.000 description 18
239000000047 product Substances 0.000 description 18
108700012941 GNRH1 Proteins 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 5
102000004196 processed proteins & peptides Human genes 0.000 description 5
239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 4
239000005557 antagonist Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000003814 drug Substances 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
229920000858 Cyclodextrin Polymers 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
108010023617 abarelix Proteins 0.000 description 1
AIWRTTMUVOZGPW-HSPKUQOVSA-N abarelix Chemical compound C([C@@H](C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 AIWRTTMUVOZGPW-HSPKUQOVSA-N 0.000 description 1
229960002184 abarelix Drugs 0.000 description 1
159000000021 acetate salts Chemical class 0.000 description 1
RFQIWHDNNZFRBL-UHFFFAOYSA-N acetic acid;ethanol;hydrate Chemical compound O.CCO.CC(O)=O RFQIWHDNNZFRBL-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000007040 multi-step synthesis reaction Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

JP2003556430A 2001-12-29 2002-12-23 ペプチド精製 Expired - Fee Related JP4378173B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE0104462A SE0104462D0 (sv)	2001-12-29	2001-12-29	Peptide purifcation (Peptidrening)
PCT/IB2002/005581 WO2003055900A1 (fr)	2001-12-29	2002-12-23	Purification de peptide

Publications (3)

Publication Number	Publication Date
JP2005515217A JP2005515217A (ja)	2005-05-26
JP2005515217A5 true JP2005515217A5 (fr)	2005-12-22
JP4378173B2 JP4378173B2 (ja)	2009-12-02

Family

ID=20286556

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2003556430A Expired - Fee Related JP4378173B2 (ja)	2001-12-29	2002-12-23	ペプチド精製

Country Status (18)

Country	Link
US (1)	US7057014B2 (fr)
EP (1)	EP1468009B1 (fr)
JP (1)	JP4378173B2 (fr)
KR (1)	KR100880828B1 (fr)
CN (1)	CN1272341C (fr)
AT (1)	ATE449784T1 (fr)
AU (1)	AU2002347550B2 (fr)
CA (1)	CA2471717C (fr)
DE (1)	DE60234535D1 (fr)
DK (1)	DK1468009T3 (fr)
ES (1)	ES2350880T3 (fr)
IL (2)	IL162789A0 (fr)
NO (1)	NO329024B1 (fr)
NZ (1)	NZ534151A (fr)
RU (1)	RU2303040C2 (fr)
SE (1)	SE0104462D0 (fr)
WO (1)	WO2003055900A1 (fr)
ZA (1)	ZA200405135B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1359722A1 (fr) *	2002-03-27	2003-11-05	BRITISH TELECOMMUNICATIONS public limited company	Système et procédé pour transmettre des flux de données
MX2007008781A (es)	2005-01-21	2007-09-11	Astex Therapeutics Ltd	Compuestos farmaceuticos.
WO2008044041A1 (fr)	2006-10-12	2008-04-17	Astex Therapeutics Limited	Combinaisons pharmaceutiques
EP2073807A1 (fr)	2006-10-12	2009-07-01	Astex Therapeutics Limited	Combinaisons pharmaceutiques
EP2062909A1 (fr) *	2007-11-21	2009-05-27	SOLVAY (Société Anonyme)	Production de peptides et procédé de purification
US9051349B2 (en)	2007-11-21	2015-06-09	Alba Therapeutics Corporation	Larazotide acetate compositions
EP2280993A1 (fr) *	2008-05-15	2011-02-09	Novo Nordisk A/S	Purification de peptides préparés par synthèse en phase solide
WO2010115916A1 (fr) *	2009-04-10	2010-10-14	F. Hoffmann-La Roche Ag	Procédé d'isolement d'un peptide thérapeutique
CN107753954A (zh)	2012-12-13	2018-03-06	免疫医疗公司	功效改进且毒性降低的抗体与sn‑38的免疫缀合物的剂量
WO2015012904A2 (fr) *	2012-12-13	2015-01-29	Immunomedics, Inc.	Immunoconjugués anticorps-sn-38 avec un lieur cl2a
US9931417B2 (en)	2012-12-13	2018-04-03	Immunomedics, Inc.	Antibody-SN-38 immunoconjugates with a CL2A linker
AU2014293670B2 (en) *	2013-07-23	2019-08-01	Immunomedics, Inc.	Antibody-SN-38 immunoconjugates with a CL2A linker
AU2017257254B2 (en)	2016-04-27	2022-02-24	Immunomedics, Inc.	Efficacy of anti-Trop-2-SN-38 antibody drug conjugates for therapy of tumors relapsed/refractory to checkpoint inhibitors
EP3600283A4 (fr)	2017-03-27	2020-12-16	Immunomedics, Inc.	Traitement de cancer du sein triple négatif exprimant la trop-2 avec du sacmuzumab govitécan et un inhibiteur de rad51
US10799597B2 (en)	2017-04-03	2020-10-13	Immunomedics, Inc.	Subcutaneous administration of antibody-drug conjugates for cancer therapy
CN113952944B (zh) *	2021-12-23	2022-03-29	浙江湃肽生物有限公司深圳分公司	一种纯化九肽-1的方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8317697D0 (en) *	1983-06-29	1983-08-03	Shell Int Research	Dissolution of peptides in non-aqueous and mixed non-aqueous/aqueous solvents
DE4001238A1 (de) *	1990-01-18	1991-07-25	Basf Ag	Verfahren zur anreicherung bzw. reinigung von biomolekuelen
DE19544212A1 (de) *	1995-11-28	1997-06-05	Asta Medica Ag	Neue LH-RH-Antagonisten mit verbesserter Wirkung
DE19813849A1 (de) *	1998-03-27	1999-09-30	Degussa	Verfahren zur einstufigen Umsalzung und Aufreinigung von Oligopeptiden
EP0998940A1 (fr)	1998-09-30	2000-05-10	Laboratoire Theramex	Compositions pharmaceutiques à base de alpha-cyclodextrine pour administration orale d'analogues de LH-RH
DE19911771B4 (de) *	1999-03-17	2006-03-30	Zentaris Gmbh	LHRH-Antagonist, Verfahren zu seiner Herstellung und seiner Verwendung

2001
- 2001-12-29 SE SE0104462A patent/SE0104462D0/xx unknown
2002
- 2002-12-23 AU AU2002347550A patent/AU2002347550B2/en not_active Ceased
- 2002-12-23 CN CNB028283481A patent/CN1272341C/zh not_active Expired - Fee Related
- 2002-12-23 US US10/500,302 patent/US7057014B2/en not_active Expired - Fee Related
- 2002-12-23 EP EP02783479A patent/EP1468009B1/fr not_active Expired - Lifetime
- 2002-12-23 WO PCT/IB2002/005581 patent/WO2003055900A1/fr not_active Ceased
- 2002-12-23 RU RU2004119965/04A patent/RU2303040C2/ru not_active IP Right Cessation
- 2002-12-23 NZ NZ534151A patent/NZ534151A/en not_active IP Right Cessation
- 2002-12-23 CA CA2471717A patent/CA2471717C/fr not_active Expired - Fee Related
- 2002-12-23 DK DK02783479.5T patent/DK1468009T3/da active
- 2002-12-23 JP JP2003556430A patent/JP4378173B2/ja not_active Expired - Fee Related
- 2002-12-23 AT AT02783479T patent/ATE449784T1/de not_active IP Right Cessation
- 2002-12-23 KR KR1020047010363A patent/KR100880828B1/ko not_active Expired - Fee Related
- 2002-12-23 DE DE60234535T patent/DE60234535D1/de not_active Expired - Lifetime
- 2002-12-23 IL IL16278902A patent/IL162789A0/xx unknown
- 2002-12-23 ES ES02783479T patent/ES2350880T3/es not_active Expired - Lifetime
2004
- 2004-06-28 ZA ZA2004/05135A patent/ZA200405135B/en unknown
- 2004-06-29 IL IL162789A patent/IL162789A/en not_active IP Right Cessation
- 2004-07-16 NO NO20043046A patent/NO329024B1/no not_active IP Right Cessation

Publication	Publication Date	Title
JP4378173B2 (ja)	2009-12-02	ペプチド精製
JP2005515217A5 (fr)	2005-12-22
JP5850458B2 (ja)	2016-02-03	デガレリックスの製造方法
CA1315229C (fr)	1993-03-30	Procede de purification chromatographique
EP2076528B1 (fr)	2010-12-08	Procédés de purification de composés de type échinocandine
CN101305018A (zh)	2008-11-12	合成卡泊芬净的方法和中间体
TWI488862B (zh)	2015-06-21	Separation and Purification of Cyclohexyl Compounds and Their Salts
CN100584859C (zh)	2010-01-27	制备棘白菌素衍生物的方法
JP2980689B2 (ja)	1999-11-22	シクロスポリンａの製造方法
SU1396970A3 (ru)	1988-05-15	Способ получени производных гонадолиберина
EP0955308A1 (fr)	1999-11-10	Procédé de résalification et purification de peptides en une seule étape
US4512923A (en)	1985-04-23	Luteinizing and follicle stimulating hormones and process for the preparation thereof
WO2016012938A2 (fr)	2016-01-28	Procédé amélioré de préparation du linaclotide amorphe
HU201120B (en)	1990-09-28	Chromatographic process for cleaning fermentation lipopeptide products
EP1189932A1 (fr)	2002-03-27	Derives de l'echinocandine, leur procede de preparation et leur application comme antifongiques
JPS60155197A (ja)	1985-08-15	アルギニン　バソプレツシンきつ抗薬の新規誘導体
EP1189933B1 (fr)	2003-04-09	Derives de l'echinocandine, leur procede de preparation et leur application comme antifongiques
DE2648829A1 (de)	1977-06-16	Nonapeptide, verfahren zu deren herstellung und diese enthaltende arzneimittel
HK1076112B (en)	2007-02-09	Peptide purification
CN1763084B (zh)	2010-04-21	高纯度环孢菌素a的制备方法
MX2008006361A (en)	2008-10-03	Purification processes of echinocandin-type compounds